SYNTHESIS 



hydroxy-4-hyciroxymethyl-2-methylpyridine, by the following route : 

 CHjOMe CHjOMe 



HO 

 CH 



CH2OH SOCI2 Ho/\|CH2Cl NH3 

 I II " 



" TH 



3^^ CH3^^ 



CHaOMe CH2OH 



PH ll TTT i 'I 



and showed that it differed from pyridoxamine in its chemical be- 

 haviour and in the absence of growth-promoting activity. They also 

 showed that the oxime of pyridoxal yielded pyridoxamine on catalytic 

 hydrogenation, thus establishing the fact that the formyl group was 

 in the 4- and not the 5-position. The isomeric aldehyde, 5-formyl-3- 

 hydroxy-4-hydroxymethyl-2-methylpyridine, was synthesised and 

 shown to be different from pyridoxal and to have no significant growth- 

 promoting properties. 



References to Section 3 



1. R. Kuhn and G. Wendt, Ber., 1938, 71, 1534. 



2. R. Kuhn and G. Wendt, ihid., 1939, 72, 305. 



3. O. Folin and W. Denis, /. Biol. Chem., 1912, 12, 239 ; 1915, 22, 305. 



4. R. Kuhn, G. Wendt and K. Westphal, Ber., 1939, 72, 310. 



5. R. Kuhn, H. Andersag, K. Westphal and G. Wendt, ibid., 309. 



6. E. T. Stiller, J. C. Keresztesy and J. R. Stevens, /. Amer. Chem, 



Soc, 1939, 61, 1237. 



7. S. A. Harris, E. T. Stiller and K. Folkers, ibid., 1242. 



8. E. E. Snell, B. M. Guirard and R. J. Williams, /. Biol. Chem., 



1942, 143, 519. 



9. E. E. Snell, ibid., 1944, 154, 313 ; /. Amer. Chem. Soc, 1944 66, 



2082 ; Research Corp. and E. E. Snell, B.P. 603289, 603290. 



10. E. E. Snell, ibid., 1945, 67, 194. 



11. S. A. Harris, D. Heyl, K. Folkers and E. E. Snell, /. Biol. Chem., 



1944, 154, 315 ; S. A. Harris, D. Heyl and K. Folkers, /. Amer. 

 Chem. Soc, 1944, 66, 2088. 



4. SYNTHESIS OF PYRIDOXINE 



Pyridoxine was synthesised independently by the two groups of 

 workers mentioned above and, in addition, by a group of Japanese 

 workers. 



S. A. Harris and K. Folkers ^ used the method represented by the 

 following series of transformations : 



301 



